A Simple Route to a Pyridinyl[2.2]paracyclophane

A Simple Route to a Pyridinyl[2.2]paracyclophane

4‐Acetyl[2.2]paracyclophane (1) is converted into the nitrone 2 by treatment with N‐methylhydroxylamine·hydrochloride. When 2 is reacted with (E)‐1,2‐dibenzoylethene (4) the pyridinyl[2.2]paracyclophane 13 is formed in a novel condensation reaction. The structures of 2 and 13, and the mechanism of f...

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Veröffentlicht in:European journal of organic chemistry 2005-01, Vol.2005 (1), p.68-71
Hauptverfasser: Hopf, Henning, Aly, Ashraf A., Swaminathan, Vijay Narayanan, Ernst, Ludger, Dix, Ina, Jones, Peter G.
Format: Artikel
Sprache:eng
Schlagworte:
Chiral cyclophanes
Cycloadditions
Dipolar cycloadditions
Nitrones
X-ray diffraction
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Zusammenfassung:4‐Acetyl[2.2]paracyclophane (1) is converted into the nitrone 2 by treatment with N‐methylhydroxylamine·hydrochloride. When 2 is reacted with (E)‐1,2‐dibenzoylethene (4) the pyridinyl[2.2]paracyclophane 13 is formed in a novel condensation reaction. The structures of 2 and 13, and the mechanism of formation of the latter are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400633